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Formula | C21H30O3 |
Molar mass | 330.468 g·mol−1 |
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3'-Hydroxy-THC (3'-OH-Δ9-THC) is a minor active metabolite of THC, the main psychoactive component of cannabis. It is one of a number of metabolites of THC hydroxylated on the pentyl side chain, but while the other side-chain hydroxyl isomers are much weaker or inactive, the S enantiomer of 3'-OH-THC is several times more potent than THC itself, and while it is produced in smaller amounts than other active metabolites such as 11-Hydroxy-THC and 8,11-Dihydroxy-THC, it is thought to contribute to the overall pharmacological profile of cannabis.[1][2][3][4][5]
See also
References
- ^ Widman M, Nordqvist M, Dollery CT, Briant RH. Metabolism of Δ1-tetrahydrocannabinol by the isolated perfused dog lung. Comparison with in vitro liver metabolism. Journal of Pharmacy and Pharmacology 1975; 27: 842-848. doi:10.1111/j.2042-7158.1975.tb10227.x
- ^ Agurell S. et al. (1976) Cannabinoids: Metabolites Hydroxylated in the Pentyl Side Chain. In: Nahas G.G., Paton W.D.M., Idänpään-Heikkilä J.E. (eds) Marihuana. Springer, Berlin, Heidelberg. doi:10.1007/978-3-642-51624-5_12
- ^ Handrick GR, Duffley RP, Lambert G, Murphy JG, Dalzell HC, Howes JF, et al. (December 1982). "3'-Hydroxy- and (+/-)-3',11-dihydroxy-delta 9-tetrahydrocannabinol: biologically active metabolites of delta 9-tetrahydrocannabinol". Journal of Medicinal Chemistry. 25 (12): 1447–50. doi:10.1021/jm00354a011. PMID 6296389.
- ^ Martin BR, Kallman MJ, Kaempf GF, Harris LS, Dewey WL, Razdan RK (July 1984). "Pharmacological potency of R- and S-3'-hydroxy-delta 9-tetrahydrocannabinol: additional structural requirement for cannabinoid activity". Pharmacology, Biochemistry, and Behavior. 21 (1): 61–5. doi:10.1016/0091-3057(84)90131-x. PMID 6087379. S2CID 45091289.
- ^ Huestis MA (August 2007). "Human cannabinoid pharmacokinetics". Chemistry & Biodiversity. 4 (8): 1770–804. doi:10.1002/cbdv.200790152. PMC 2689518. PMID 17712819.